Patent GB-517631-A (GB)
Title: New water repellent agents
IPC: D06M13/46
Filed: 1938-08-02
Abstract: 517,631. Quaternary ammonium compounds; softening, waterproofing and anti-crease treatments for textiles. ROGERS, M. A. T., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. Aug. 2, 1938, Nos. 22850/38, 22851/38, 7097/39 and 7099/39. [Classes 2 (iii) and 15 (ii)] [Also in Group VIII] Quaternary ammonium salts are made by combining with aliphatic or beterocyclic tertiary amines halogenmethyl compounds of the formula where R is an aliphatic radicle of at least 7 carbon atoms, A is a divalent organic radicle, and X is halogen- The halogenethyl compounds are made by causing the chloroformic ester of an alcohol R.OH (2 mols.) to react with a diamine NH2.A.NH 2 (1 mol.), whereby a dicarbamate of the formula RO.CO.NH.A.NH.CO.OR is formed which is then treated with a hydrogen halide or phosgene and formaldehyde or a polymer thereof, or with a dihalogenodimethyl ether, Alcohols of the formula R.OH include octyl, decyl, dodecyl, myristyl, cetyl, octadecenyl, octadecyl and ceryl alcohols, and mixtures of alcohols obtained by reduction of the acids of natural fats and oils, e.g. coconut oil, palm kernel oil or wool fat, alcohols obtainable by reduction of the esters of montanic acid or by hydrolysis of the mixed sulphuric esters obtained by sulphonation of polymerized lower olefines, and also alcohols which are likewise esters, e.g. #-hydroxyethyl stearate. A large number of suitable halogenomethyl compounds is specified, including those in which X=Cl or Br, and A=-CH2-, -CH2-CH2-, or a hexamethylene, o-, m- or p-phenylene,2-chloro- or 2-methoxy-1:4-phenylene, 6-methyl-1:3- phenylene, 1:5-naphthylene residue, or is two phenylene residues linked by an -S-, -SO-, or -CH2- group. The aliphatic or heterocyclic tertiary amines specified are trimethylamine, triethylamine, N:N<1>-tetramethylethylenediamine, dimethyl (or ethyl) cyclohexylamine, N-methylpiperidine, pyridine and alphapicoline. In examples : (1) di-octodecyl-pphenylene dicarbamate (made from octadecyl chloroformate and p-phenylenediamine) is treated with paraformaldehyde and hydrogen chloride, and the dichlormethyl compound obtained is combined with pyridine to form di-octodecyl-N:-Wdi-(N<1>-chloropyridinomethyl) p-phenylene dicarbamate ; similarly dipyridinium dichlorides may be made in which A is o- or m-phenylene, ethylene, hexamethylene, etc., or in which R is dodecyl, amd (2) the dichlormethyl compounds made from diocatadecyl - m - phenylenedicarbamate or dioctadecyl-ethylene-dicarbamate are combined with triethylamine, trimethylamine, or dimethylcyclohexylamine. The products may be used for softening or waterproofing textile materials of animal or vegetable origin, or composed of regenerated cellulose or cellulose esters or ethers, by impregnating the materials with the quaternary salts in solution or suspension in water or an organic liquid, the impregnated material being subsequently subjected to a short heat treatment to decompose the quaternary salt. Examples are given of the application of this process to calico, viscose, cellulose acetate and wool delaine fabrics. The quaternary salts may also be applied to natural or regenerated cellulose textile materials in conjunction with anti-creasing treatments, by treating the materials with a solution or suspension of the quaternary salt in water or an organic liquid before, simultaneously with, or after a treatment with a medium comprising a partly condensed resinous condensation product derived from an aldehyde and urea, thiourea or derivative thereof, or a phenol or an amino-1:35- triazine under neutral, acid or alkaline conditions, or with the components of such a resinous condensation product, followed by drying and finally by a short heat treatment to decompose the quaternary salt and insolubilize the resin. Examples are given of the application of this treatment to viscose and mercerized cotton fabrics. Specifications 291,473, 291,474, 304,900, [all in Class 2 (iii)], 431,703, 449,243, 458,877, 466,015, 466,817, 477,991, 485,198, 493,920, 495,025, 497,856, and 498,287 are referred to.